Various adenosine derivatives are claimed having desirable ratio of affinities at A1 or A2 receptors and highly desirable central nervous system and cardiovascular activities, such as analgesic, antipsychotic, sedative, or antihypertensive, as well as immunoinflammatory activity in copending applications. However, in each case the substituents do not teach the benzothien-3-yl; benzothien-3-yl, S-oxide; and benzothien-3-yl, S,S-dioxide adenosines of the present invention. For example, U.S. Ser. No. 665,219, now U.S. Pat. No. 4,593,019, discloses N.sup.6 -tricyclic adenosines, U.S. Ser. No. 665,195, now abandoned, discloses N.sup.6 -acenaphthyl adenosines, U.S. Ser. No. 665,197, now abandoned, discloses N.sup.6 -benzopyrano- and benzothipyrano adenosines, U.S. Ser. No. 665,218, now abandoned discloses N.sup.6 -tetrahydronaphthyl adenosines, U.S. Ser. No. 665,216, now abandoned, discloses N.sup.6 -bicyclo[2.2.1]heptyl adenosines, U.S. Ser. No. 665,229, now abandoned, discloses N.sup.6 -dihydroxypropyl adenosines, U.S. Ser. No. 665,230 discloses (s)-N.sup.6 -2-hydroxypropyl adenosines, U.S. Ser. No. 665,217, now abandoned, discloses N.sup.6 -substituted deoxyribose adenosines, U.S. Ser. No. 665,233, now abandoned, discloses N.sup.6 -substituted-5'-deoxy-5'-chloro adenosines, U.S. Ser. No. 665,232, now abandoned, discloses N.sup.6 -substituted-5'-deoxy-5'-methylthioadenosines and U.S. Ser. No. 558,144, now U.S. Pat. No. 4,501,735, discloses benzocycloalkyl adenosines.
Additionally, British 1,529,721 discloses an N.sup.6 -substituted adenosine containing the N.sup.6 nitrogen in a heterocyclic substituent for use as antiproliferative and coronary-circulation-active agents and French 6650M (Derwent No. 37,912) discloses N.sup.6 -alkyl, -aryl, -araalkyl, -furfuryl, and -thienyl adenosine compounds for use as antiinflammatory agents.
Finally, a German Offenlegungsschrift 2,139,107 discloses adenosine derivatives for increased coronary flow and/or increaed oxygen partial pressure in coronary venous blood and circulatory, antilipolytic, and/or hypocholesterolaemic activity. These derivatives disclose N.sup.6 -substituents of adenosine including an R'-(CH.sub.2).sub.n -NH-substituent wherein R' may include a benzothienyl group and n is 0, 1, 2, 3, or 4, but, preferably 0 or 1. Substitutions of R' groups are suggested generically but are limited to alkyls or groups attached through alkyls. The only species exemplified having a benzothienyl group has a 3-aminomethylbenzothiophen substituent. Thus, the invention of the present disclosure is either outside the disclosure of the German reference, or provides novel compounds with activity which is not obvious from the disclosure of the reference, for example, for compounds of the present invention having in every case a --CH.sub.2 CH.sub.2 linkage between the benzothienyl group and adenosine residue.
The compounds of the instant invention are adenosine analogs having some of the same activity as adenosine, but having a significantly longer duration of action. A distinguishing feature of these compounds from other adenosine analogs previously described, is the discovery that benzothien-3-yl adenosine; benzothien-3-yl adenosine, S-oxide; and benzothien-3-yl adenosine, S,S-dioxide compounds of the present invention have favourable ratio of affinities at A1 and A2 receptors and highly desirable central nervous system and cardiovascular activities, such as analgesic, antipsychotic, sedative, or antihypertensive. In addition, these adenosine compounds also have immunoinflammatory activity.